Complement pathway modulators and uses thereof
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example 23
2-({[(2S,4R)-1-(1-Carbamoyl-1H-indol-3-ylcarbamoyl)-4-fluoro-pyrrolidine-2-carbonyl]-amino}-methyl)-benzoic acid
[1717]
[1718]To a solution of 2-({[(2S,4R)-1-(1-carbamoyl-1H-indol-3-ylcarbamoyl)-4-fluoro-pyrrolidine-2-carbonyl]-amino}-methyl)-benzoic acid tert-butyl ester (prepared according to Scheme D1 using 2-aminomethyl-benzoic acid tert-butyl ester) (76 mg, 0.145 mm) in CH2Cl2 (1 mL) was added TFA (168 μl, 2.18 mmol) and the resulting solution was stirred at RT overnight. The crude mixture was concentrated to give a solid which was suspended in Et2O and filtered to give the desired material. MS (LC-MS): 468.1 [M+H]+, 490.1 [M+Na]+, 957.2 [2M+Na]+, 466.1 [M−H]−, 423.1 [M−CONH2]−, tR (HPLC conditions a): 2.64 min.
example 24
2-({[(2S,4R)-1-(1-Carbamoyl-1H-indol-3-ylcarbamoyl)-4-fluoro-pyrrolidine-3-carbonyl]-amino}-methyl)-benzoic acid
[1719]
[1720]To a solution of 3-({[(2S,4R)-1-(1-carbamoyl-1H-indol-3-ylcarbamoyl)-4-fluoro-pyrrolidine-2-carbonyl]-amino}-methyl)-benzoic acid tert-butyl ester (prepared according to Scheme D1 using 3-aminomethyl-benzoic acid tert-butyl ester) (21 mg, 0.04 mmol) in CH2Cl2 (0.5 mL) was added TFA (31 μl, 0.4 mmol) and the solution was stirred at RT for 24 h. The solvent was concentrated and the crude residue was purified by preparative HPLC (C18-ODB, 5 μm, 19×50 mm, waters, eluent: CH3CN / H2O+0.1% HCOOH flow: 20 mL / min, standard 20% method) to give after lyophilization of the purified fractions the desired material. MS (LC-MS): 468 [M+H]+, 490 [M+Na]+, 466 [M−H]−, 423.0 [M−CONH2]−; tR (HPLC conditions a): 2.57 min.
example 25
(2S,3S)-2-{[(2S,4R)-1-(1-Carbamoyl-1H-indol-3-ylcarbamoyl)-4-fluoro-pyrrolidine-2-carbonyl]-amino}-3-methyl-pentanoic acid
[1721]
[1722]To a suspension of (2S,3S)-2-{[(2S,4R)-1-(1-carbamoyl-1H-indol-3-ylcarbamoyl)-4-fluoro-pyrrolidine-2-carbonyl]-amino}-3-methyl-pentanoic acid tert-butyl ester Example 15 (64 mg, 0.127 mmol) in CH2Cl2 (1 mL) was added TFA (97 μl, 1.27 mmol) and the resulting solution was stirred at RT for 20 h. TFA (1.27 mmol) was added again to ensure completion of the reaction. CH2Cl2 was concentrated and the crude residue was purified by preparative HPLC (C18-ODB, 5 μm, 19×50 mm, waters, eluent: CH3CN / H2O+0.1% HCOOH flow: 20 mL / min, standard 20% method) to give after lyophilization of the purified fractions the desired material which was dissolved in CH3CN and was purified again on trimethylaminopropyl cartridge (Mega Bond Elut-SAX, 1 g, from Varian, conditioned with 20 mL of CH3CN). The column was eluted with CH3CN and the compound was finally released with 10 mL o...
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